CN113512048B - An organic compound and an organic light-emitting device using the same - Google Patents
An organic compound and an organic light-emitting device using the same Download PDFInfo
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- CN113512048B CN113512048B CN202110780568.XA CN202110780568A CN113512048B CN 113512048 B CN113512048 B CN 113512048B CN 202110780568 A CN202110780568 A CN 202110780568A CN 113512048 B CN113512048 B CN 113512048B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
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- 230000005525 hole transport Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
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- FMKGJQHNYMWDFJ-CVEARBPZSA-N 2-[[4-(2,2-difluoropropoxy)pyrimidin-5-yl]methylamino]-4-[[(1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl]amino]pyrimidine-5-carbonitrile Chemical compound FC(COC1=NC=NC=C1CNC1=NC=C(C(=N1)N[C@H]1CC([C@H](CC1)O)(C)C)C#N)(C)F FMKGJQHNYMWDFJ-CVEARBPZSA-N 0.000 description 4
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- 229940127113 compound 57 Drugs 0.000 description 4
- BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 4
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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- MTBRQOGPXZHFAH-UHFFFAOYSA-N 3-anilino-2-pyridin-4-yl-1,5,6,7-tetrahydropyrrolo[3,2-c]pyridin-4-one Chemical compound C1(=CC=CC=C1)NC1=C(NC2=C1C(NCC2)=O)C1=CC=NC=C1 MTBRQOGPXZHFAH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- LFZAGIJXANFPFN-UHFFFAOYSA-N N-[3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-thiophen-2-ylpropyl]acetamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CCC(C=1SC=CC=1)NC(C)=O)C LFZAGIJXANFPFN-UHFFFAOYSA-N 0.000 description 2
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- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- WDBQJSCPCGTAFG-QHCPKHFHSA-N 4,4-difluoro-N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclohexane-1-carboxamide Chemical compound FC1(CCC(CC1)C(=O)N[C@@H](CCN1CCC(CC1)N1C(=NN=C1C)C(C)C)C=1C=NC=CC=1)F WDBQJSCPCGTAFG-QHCPKHFHSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- 238000005401 electroluminescence Methods 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 238000007711 solidification Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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Abstract
本发明提供一种有机化合物和使用该化合物的有机发光器件，具体涉及一种具有优异的发光效率和寿命的有机化合物以及使用该化合物的OLED器件。本发明提供的有机化合物结构如式1所示：上述的结构式中，Ar1选自取代或未取代的包含氮原子两个以上的C6～C90杂芳基、杂环基或胺系列物质；R1和R2各自独立地选自取代或未取代的C1～C20烷基、取代或未取代的C6～C30芳基、取代或未取代的C10～C30稠环基、取代或未取代的C4～C30杂芳基、取代或未取代的C13～C30胺系类物质。The present invention provides an organic compound and an organic light-emitting device using the compound, and specifically relates to an organic compound with excellent luminous efficiency and lifespan and an OLED device using the compound. The structure of the organic compound provided by the present invention is shown in Formula 1: In the above structural formula, Ar1 is selected from substituted or unsubstituted C6-C90 heteroaryl, heterocyclic or amine series substances containing two or more nitrogen atoms; R1 and R2 are each independently selected from substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 condensed ring, substituted or unsubstituted C4-C30 heteroaryl, substituted or unsubstituted C13-C30 amine series substances.
Description
Technical Field
The present invention relates to an organic compound and an organic light emitting tube device using the same, and more particularly, to an organic compound having excellent light emitting efficiency and lifetime and an OLED device using the same.
Background
With the development of multimedia technology and the improvement of informatization requirements, the requirements on the performance of panel displays are higher and higher. The OLED has a series of advantages of autonomous luminescence, low-voltage direct current drive, full solidification, wide viewing angle, rich colors and the like, and is widely paid attention to potential application in a new-generation display and illumination technology, so that the OLED has a very wide application prospect. The organic electroluminescent device is a spontaneous luminescent device, and the mechanism of OLED luminescence is that electrons and holes are respectively injected from positive and negative poles and then migrate, recombine and decay in an organic material under the action of an external electric field to generate luminescence. Typical structures of OLEDs include one or more functional layers of a cathode layer, an anode layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport layer, a hole injection layer, and an organic light emitting layer.
Although research progress of organic electroluminescence is very rapid, there are many problems to be solved, such as improvement of External Quantum Efficiency (EQE), design and synthesis of new materials with higher color purity, design and synthesis of new materials with high efficiency of electron transport/hole blocking, and the like. For the organic electroluminescent device, the luminous quantum efficiency of the device is a comprehensive reflection of various factors and is also an important index for measuring the quality of the device.
Luminescence can be classified into fluorescence luminescence and phosphorescence luminescence. In fluorescence emission, an organic molecule in a singlet excited state transitions to a ground state, thereby emitting light. On the other hand, in phosphorescence, an organic molecule in a triplet excited state transitions to a ground state, thereby emitting light.
At present, some organic electroluminescent materials have been commercially used because of their excellent properties, but as host materials in organic electroluminescent devices, it is more important to have good hole transport properties in addition to triplet energy levels higher than guest materials, preventing energy back transfer by exciton transition release. Currently, materials that have both high triplet energy levels and good hole mobility in host materials are still lacking. Therefore, how to design new host materials with better performance is always a problem to be solved by those skilled in the art.
Disclosure of Invention
An object of the present invention is to provide an organic compound having excellent light-emitting efficiency and lifetime, and an organic light-emitting device using the same.
The invention provides an organic compound, the structural formula of which is shown as 1,
In the structural formula, ar1 is selected from substituted or unsubstituted C6-C90 heteroaryl, heterocyclic group or amine series substances containing more than two nitrogen atoms;
R1 and R2 are each independently selected from the group consisting of substituted or unsubstituted C1-C20 alkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C10-C30 fused ring groups, substituted or unsubstituted C4-C30 heteroaryl groups, and substituted or unsubstituted C13-C30 amine-based materials.
Further preferred is a structure wherein Ar 1 is selected from the following structures:
Wherein R3, R4 and R5 are independently selected from hydrogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
X1, X2, X3 are independently selected from nitrogen (N) or carbon (C);
L1 is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl.
Further preferred is a structure wherein R1 and R2 are independently selected from the following structures:
Wherein R8, R9 and R10 are independently selected from one of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C4-C30 heteroaryl, or a combination thereof;
l2 is a single bond or is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C4-C30 heteroaryl.
Further preferred is that the organic compound is independently selected from the following compounds:
The invention also provides application of the heterocyclic compound in an organic light-emitting device.
Preferably, the organic light-emitting device comprises an anode, a cathode and a plurality of organic functional layers positioned between the anode and the cathode, wherein the organic functional layers contain the heterocyclic compound.
The invention has the beneficial effects that:
the invention provides a heterocyclic compound which has a structure shown in a formula 1, and the electron-rich structure in the heterocyclic compound has great influence on the photoelectric property of the whole compound molecule, thereby being beneficial to reducing unnecessary vibration energy loss and realizing high-efficiency luminous performance. By adjusting substituent groups, the compound has better thermal stability and chemical property. The heterocyclic compound disclosed by the invention is simple in preparation method, easy to obtain raw materials and capable of meeting the industrial requirements.
The heterocyclic compound is prepared into a device, particularly used as a main body material, and the device has the advantages of high luminous efficiency and long service life, and is superior to the existing common OLED device.
In the present invention, the organic electroluminescent device preferably comprises an anode, a cathode and several organic layers between the anode and the cathode, the term "organic layer" referring to all layers disposed between the anode and the cathode in the organic electroluminescent device. The organic layer may be a layer having a hole property and a layer having an electron property. For example, the organic layer includes one or more of a hole injection layer, a hole transport layer, a layer having both hole injection and hole transport, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a layer having both electron transport and electron injection.
In the present invention, the hole injection layer, the hole transport layer, and the hole injection and transport layer may be formed of a conventional hole injection material, a conventional hole transport material, or a conventional hole injection and transport material, and may include an electron-generating material.
For example, the organic layer may include a light emitting layer including one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. In the present invention, the compound for an organic electronic device may be employed as a fluorescent host, and may also be used as fluorescent doping, and simultaneously as a fluorescent host and fluorescent doping.
In the present invention, the light emitting layer may be a red, yellow or blue light emitting layer. In the present invention, when the light-emitting layer is a light-emitting layer, the organic electroluminescent device having high efficiency, high resolution, high luminance and long life can be obtained by using the above-described organic electroluminescent device compound as a main component.
In the invention, the organic electroluminescent diode device of the organic compound is characterized in that the organic electroluminescent device comprises an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode which are sequentially deposited, wherein the organic compound is used as a main material of the light emitting layer.
The method for preparing the organic electroluminescent device according to the present invention is not particularly limited, and may be prepared using a method and materials for preparing a light emitting device, which are well known to those skilled in the art, in addition to the organic compound of formula 1.
Detailed Description
The invention is further described in connection with the following embodiments in order to make the technical means, the creation features, the achievement of the purpose and the effect of the invention easy to understand.
1. Synthesis of intermediate 1-1-1
After adding O-nitrophenol (10.81 g, 40 mmol), cu 2 O (2.84 g, 20 mmol) and 1, 3-dibromo-5-chlorobenzene (20 mmol, 3.10 mmol) to a pyridine solvent at room temperature under nitrogen, the reaction was refluxed for 12 hours. When the reaction was complete, the temperature of the reaction was cooled to room temperature, and 1M-HCl aqueous solution was added, followed by extraction with diethyl ether and washing with water. A small amount of water was removed with anhydrous MgSO 4, filtered under reduced pressure, then the organic solvent was concentrated, and the resultant product was separated by column chromatography to obtain the desired intermediate a (5.45 g, yield: 65%). LC-MS: M/Z417.98 (M+).
2. Synthesis of intermediates 1-2-1 to 7-4-1
The method for synthesizing the intermediate 1-1-1 synthesizes the compound intermediate 2-1-1 to 7-1-1.
3. Synthesis of intermediate 1-1-2
To a 250 ml reaction flask was added 295-3 (2.09 g, 5.00 mmol) and triethyl phosphite (2.50 g, 14.70 mmol) and reacted overnight at 145℃under nitrogen. The reaction was stopped, 2M HCl was added after cooling, stirred to full white, extracted with a small amount of DCM. Separating the liquid to obtain an organic phase, and rotating the organic phase until the organic phase is oily. Over silica funnel, DCM: pe=1: 3 flushing. Spin-drying the solvent and recrystallizing to give 1-1-2 as a white powdery solid (1.06 g, 60% yield). LC-MS: M/Z354.01 (M+).
4. Synthesis of intermediates 1-2-2 to 7-4-2
The method for synthesizing the intermediate 1-1-2 synthesizes the compound intermediate 1-2-1-7-2-2.
Example 1: synthesis of Compound 2
1. Synthesis of intermediate 1-3-1
In a 500ml reaction flask was added intermediate 1-2-1 (21.79 g, 61.4 mmol), a (20.03 g, 61.4 mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K 2CO3 (17.0 g, 122.8 mmol), 1, 4-dioxane (200 ml) and water (50 ml). The reaction system is heated to 80 ℃ and reacted for 12 hours under the protection of nitrogen. After the completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was passed through a silica gel column to give intermediate 1-3-1 (25.08 g, yield 68%). LC-MS: M/Z600.14 (M+).
2. Synthesis of Compound 2
In a 250 ml three-neck flask was added intermediate 1-3-1 (12.02 g, 20 mmol), bromobenzene (53.14 g, 21.0 mmol), tris (dibenzylideneacetone) dipalladium (4 mol%), tri-t-butylphosphine (8 mol%), potassium t-butoxide (3.8 g, 33.6 mmol) and o-xylene (80 ml). The reaction system is heated to 120 ℃ and reacted for 12 hours under the protection of nitrogen. After the completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product, which was passed through a silica gel column to give compound 2 (9.34 g, yield 62%). LC-MS: M/Z752.21 (M+).
Example 2: synthesis of Compound 5
1. Synthesis of intermediate 13-1
Compound 5 was synthesized by the method of reference example 2 to give compound 5 (10.61 g, yield 68%). LC-MS: M/Z779.22 (M+).
Example 3: synthesis of Compound 57
1. Synthesis of intermediate 13-1
Compound 57 was synthesized by the method of reference example 2 to yield compound 57 (8.53 g, yield 63%). LC-MS: M/Z676.18 (M+).
Example 4: synthesis of Compound 73
Compound 73 was synthesized by the method of reference example 2 to give compound 73 (8.80 g, yield 65%). LC-MS: M/Z676.18 (M+).
Example 5: synthesis of Compound 114
Compound 114 was synthesized by the method of reference example 2 to yield compound 114 (9.88 g, 69%). LC-MS: M/Z715.21 (M+).
Example 6: synthesis of Compound 199
Compound 199 was synthesized by the method of reference example 2 to give compound 199 (8.26 g, yield 61%). LC-MS: M/Z676.17 (M+).
Device embodiments
(I) Evaluation of light emitting material device
The organic layer compounds used in the device examples are shown below:
1. First embodiment
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. The patterned ITO glass substrate is then washed.
The substrate is then placed in a vacuum chamber. The standard pressure was set at 1X 10-6 Torr. Thereafter on the ITO substrate with HILHI-2HTL-1Compound 2+RD-1 ((5%)ET-1LiFAnd AlSequentially forming layers of organic material.
2. Second embodiment
An organic light-emitting device of the second embodiment was produced by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 5 instead of compound 2 of the first embodiment.
3. Third embodiment
An organic light-emitting device of the third embodiment was produced by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 57 only by compound 2 of the first embodiment.
4. Fourth embodiment
An organic light-emitting device of the fourth embodiment was produced by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 73 from compound 2 of the first embodiment.
5. Fifth embodiment
An organic light-emitting device of the fifth embodiment was produced by the same method as that of the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with compound 114 by compound 2 of the first embodiment.
6. Sixth embodiment
The organic light emitting device of the fifth embodiment was prepared by the same method as the first embodiment described above, except that the host material layer of the organic light emitting device was replaced with compound 199 instead of compound 2 of the first embodiment.
7. Comparative example 1
An organic light-emitting device of comparative example was prepared by the same method as the first embodiment described above, except that the host material layer of the organic light-emitting device was replaced with the compound RH1 from the compound 2 of the first embodiment.
8. Comparative example 2
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH2 instead of the compound 2 of the first embodiment.
9. Comparative example 3
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH3 instead of the compound 2 of the first embodiment.
10. Comparative example 4
An organic light-emitting device of comparative example was prepared by the same method as the above-described first embodiment, except that the host material layer of the organic light-emitting device was replaced with the compound RH4 instead of the compound 2 of the first embodiment.
The fabricated organic light emitting device was tested for voltage, efficiency and lifetime under a current condition of 10mA/cm 2.
Table 1 shows the results of performance tests of the organic light emitting devices prepared in examples and comparative examples of the present invention.
TABLE 1
As shown in table 1, the device also operates efficiently at the same voltage. And the current efficiency and lifetime of the embodiments are significantly increased compared to the comparative examples.
The foregoing has outlined the basic principles, features, and advantages of the present invention. It will be understood by those skilled in the art that the present invention is not limited to the embodiments described above, and that the above embodiments and descriptions are merely illustrative of the principles of the present invention, and various changes and modifications may be made without departing from the spirit and scope of the invention, which is defined in the appended claims.
Claims (4)
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